Hey Cowboys,
Happy DotDev Day 2! We’re running around and meeting the community IRL, so the show today will be our greatest hits— 3 previous Ecomm Cowboy conversations that went viral. You’ll hear from:
Zach Stuck, Mars Men - The Strategy to Scale
Bill D’Alessandro, FoodScience - Smart Business Debt vs. Cash Advances
Sam Chai, Humankind - The Zero Churn Customer Experience
Missed yesterdays stream from DotDev? Here’s the roundup 👇
Harley Finkelstein: “Agentic commerce is here.”
President of Shopify, Harley Finkelstein, came on Ecomm Cowboy yesterday while live at DotDev. Yeehaw!
We discussed how agentic commerce is fundamentally merit-based. He argued this shift will disproportionately benefit long-tail merchants and small, entrepreneurial developer teams (running “armies of agents”) who can now build hugely impactful products.
Harley framed Shopify as his life's work and the "world's entrepreneurship company," rooted in his own immigrant background and a community defined by a high "give-a-shit quotient."
What a guy. You can watch Harley’s full interview here.
The Future of Shopify and Ecomm
We had a stacked list of NINE in-person conversations yesterday.
Adam Ellington (CCO, Overdose)
“Real AI transformation is top-down change management, which is why Overdose scrapped the Slack-channel playbook and gave every leader a mandate to own AI in their discipline.”
Vanessa Nugent (Founder & CEO, Allure Commerce)
“In luxury, the more technology you use the less anyone should see it, so every optimization runs in the back while a human delivers the moment.”
Tamir Eden (Co-founder, 40RTY)
“Brands still own the trust, so 40RTY builds agentic stores that keep the brand's look but swap the CMS for an LLM that adapts the whole experience to shopper intent in under three seconds.”
Atlee Clark (VP of Partnerships, Shopify)
“Shopify cut app review time from 40 days to four and rebuilt partner incentives so agencies and developers share in merchant success through ‘collaborative competition.’“
Helen Mou (Director of Product, Retail, Shopify)
“The job of retail isn't the transaction but expression, turning stores into community hubs and points of view rather than checkout counters.”
Vanessa Lee (VP of Product, Shopify)
“Agentic shopping converts 80% better than organic search, but every era still runs on the same fundamental— trust underpins every transaction.”
Eytan Seidman (VP of Product, Shopify)
“New Sidekick app extensions let apps plug their data and actions directly into Shopify's assistant, turning it into a platform where honest builders win.”
Ben Sehl (Director of Product, Online Store, Shopify)
“A modernized Liquid architecture rebuilds themes for the agents now writing most storefront code, on the thesis that a great developer experience is a great agent experience.”
Ilya Grigorik (Distinguished Engineer, Shopify)
“Rather than writing a rulebook for commerce, UCP is a protocol that lets merchants and agents negotiate on what they both support—paired with a free, internet-scale Global Catalog Shopify spent over $100M building.”
Hear everything these experts are said on the YouTube video. And let us know what you think was the most insightful. Simply respond to this email and we’ll say hi.
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What is Ecomm Cowboy?
Ecomm Cowboy is the go-to live show for ecomm operators, breaking down the latest DTC, retail, and AI news while interviewing the founders and executives building today's fastest-growing brands.
You can find our work on YouTube, X, and LinkedIn.
Have questions or want to come on the show? Simply reply to this email, we’re happy to chat.
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See you in the stream,
Ecomm Cowboy Team